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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:23 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030847
Secondary Accession Numbers
  • HMDB30847
Metabolite Identification
Common NameAromadendrin
DescriptionAromadendrin, also known as dihydrokaempferol, belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Thus, aromadendrin is considered to be a flavonoid. Aromadendrin has been detected, but not quantified in, several different foods, such as dates (Phoenix dactylifera), lovages (Levisticum officinale), chicory roots (Cichorium intybus var. sativum), summer savories (Satureja hortensis), and shiitakes (Lentinus edodes). This could make aromadendrin a potential biomarker for the consumption of these foods. Aromadendrin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Aromadendrin.
Structure
Data?1563862047
Synonyms
ValueSource
(+)-AromadendrinChEBI
(2R,3R)-DihydrokaempferolChEBI
DihydrokaempferolChEBI
(+)-DihydrokaempferolKegg
(+)-trans-3,4',5,7-TetrahydroxyflavanoneHMDB
(2R,3R)-2,3-dihydro-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
AromadendrolHMDB
KaturaninHMDB
AromadedrinMeSH, HMDB
dihydro-KaempferolMeSH, HMDB
dihydro-KempferolMeSH, HMDB
DihydrokempferolMeSH, HMDB
3,4',5,7-TetrahydroxyflavanonePhytoBank
3,4’,5,7-TetrahydroxyflavanonePhytoBank
(+)-(2R,3R)-DihydrokaempferolPhytoBank
(2R,3R)-3,4',5,7-TetrahydroxyflavanonePhytoBank
(2R,3R)-3,4’,5,7-TetrahydroxyflavanonePhytoBank
(2R,3R)-KaturaninPhytoBank
AromadendrinPhytoBank
AromadendrinePhytoBank
Chemical FormulaC15H12O6
Average Molecular Weight288.2522
Monoisotopic Molecular Weight288.063388116
IUPAC Name(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(+)-dihydrokaempferol
CAS Registry Number480-20-6
SMILES
O[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1
InChI KeyPADQINQHPQKXNL-LSDHHAIUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative Parents
Substituents
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanonol
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point247 - 249 °CNot Available
Boiling Point638.00 to 639.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21360 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.860 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.23ALOGPS
logP2.12ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.63 m³·mol⁻¹ChemAxon
Polarizability28.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.53731661259
DarkChem[M-H]-170.90531661259
DeepCCS[M+H]+168.06230932474
DeepCCS[M-H]-165.70430932474
DeepCCS[M-2H]-199.91430932474
DeepCCS[M+Na]+175.07230932474
AllCCS[M+H]+167.232859911
AllCCS[M+H-H2O]+163.532859911
AllCCS[M+NH4]+170.732859911
AllCCS[M+Na]+171.732859911
AllCCS[M-H]-165.932859911
AllCCS[M+Na-2H]-165.432859911
AllCCS[M+HCOO]-164.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AromadendrinO[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C14080.3Standard polar33892256
AromadendrinO[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C12867.8Standard non polar33892256
AromadendrinO[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C12912.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aromadendrin,1TMS,isomer #1C[Si](C)(C)O[C@H]1C(=O)C2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C12843.8Semi standard non polar33892256
Aromadendrin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)[C@H](O)[C@@H](C3=CC=C(O)C=C3)OC2=C12895.0Semi standard non polar33892256
Aromadendrin,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)[C@H](O)[C@@H](C1=CC=C(O)C=C1)O22901.3Semi standard non polar33892256
Aromadendrin,1TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C(=O)[C@@H]2O)C=C12876.0Semi standard non polar33892256
Aromadendrin,2TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)[C@H](O[Si](C)(C)C)[C@@H](C1=CC=C(O)C=C1)O22825.6Semi standard non polar33892256
Aromadendrin,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)[C@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C=C3)OC2=C12757.2Semi standard non polar33892256
Aromadendrin,2TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C(=O)[C@@H]2O[Si](C)(C)C)C=C12731.7Semi standard non polar33892256
Aromadendrin,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C(=O)[C@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C12830.6Semi standard non polar33892256
Aromadendrin,2TMS,isomer #5C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)[C@@H]2O)C=C12849.5Semi standard non polar33892256
Aromadendrin,2TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)[C@@H]2O)C=C12826.4Semi standard non polar33892256
Aromadendrin,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)[C@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C12732.8Semi standard non polar33892256
Aromadendrin,3TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)[C@@H]2O[Si](C)(C)C)C=C12739.7Semi standard non polar33892256
Aromadendrin,3TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)[C@@H]2O[Si](C)(C)C)C=C12720.0Semi standard non polar33892256
Aromadendrin,3TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)[C@@H]2O)C=C12793.4Semi standard non polar33892256
Aromadendrin,4TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)[C@@H]2O[Si](C)(C)C)C=C12783.2Semi standard non polar33892256
Aromadendrin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C(=O)C2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C13137.8Semi standard non polar33892256
Aromadendrin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)[C@H](O)[C@@H](C3=CC=C(O)C=C3)OC2=C13157.8Semi standard non polar33892256
Aromadendrin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)[C@H](O)[C@@H](C1=CC=C(O)C=C1)O23166.7Semi standard non polar33892256
Aromadendrin,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C(=O)[C@@H]2O)C=C13168.3Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C1=CC=C(O)C=C1)O23371.9Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C=C3)OC2=C13291.6Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C(=O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C13281.2Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)[C@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13361.6Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)[C@@H]2O)C=C13387.1Semi standard non polar33892256
Aromadendrin,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)[C@@H]2O)C=C13380.5Semi standard non polar33892256
Aromadendrin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13449.2Semi standard non polar33892256
Aromadendrin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C13467.6Semi standard non polar33892256
Aromadendrin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C13475.0Semi standard non polar33892256
Aromadendrin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)[C@@H]2O)C=C13559.4Semi standard non polar33892256
Aromadendrin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C13677.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aromadendrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1980000000-7cc958a9df81a10ae0142017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aromadendrin GC-MS (4 TMS) - 70eV, Positivesplash10-0imi-2640190000-17f316a7c4647990a2a12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aromadendrin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aromadendrin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 2V, positive-QTOFsplash10-000i-0090000000-e14b8e1e7fc48a9342822020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 4V, positive-QTOFsplash10-000i-0190000000-caa95001f74424bb52222020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 6V, positive-QTOFsplash10-000l-0390000000-8b70a51c1d08add76cf32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 9V, positive-QTOFsplash10-0f6y-0960000000-b5c81668eb25d016bb9a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 13V, positive-QTOFsplash10-0zfs-0920000000-d3910e809932fbdc13352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 16V, positive-QTOFsplash10-0zfs-0910000000-e6f229665ff43b8145a02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 21V, positive-QTOFsplash10-0pba-0900000000-c780a80ff30a1abeba782020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 26V, positive-QTOFsplash10-0pb9-2900000000-c4b467ede4839437ed7e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 31V, positive-QTOFsplash10-0aor-4900000000-c1e3fa3d2f2a0c2ba7642020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 36V, positive-QTOFsplash10-066r-7900000000-1c0136dd8c1655bec51c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 43V, positive-QTOFsplash10-014i-9600000000-5763889d46e13d2844352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 49V, positive-QTOFsplash10-014i-9400000000-a998ccc5e9ebd751af382020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin Orbitrap 59V, positive-QTOFsplash10-0gb9-9200000000-07dde11b111d2476a2312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-0udi-0900000000-68e4c8151c0f883627d92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-014j-0790000000-7f8b28dbff78e274843d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-0002-0900000000-5f1aa642fd3aeaee0a732020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-0006-0090000000-57c4f9f24ca1c1e7c2322020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-0006-9000000000-59c49d4b3fd90c1740fd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aromadendrin n/a 20V, positive-QTOFsplash10-00di-0900000000-ffdcca5bd2b965040c672020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 10V, Positive-QTOFsplash10-000i-0190000000-4ceeaed3349641593d662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 20V, Positive-QTOFsplash10-0kg9-0960000000-b54d012869a01298fd892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 40V, Positive-QTOFsplash10-0kmr-4900000000-cb8757bc53bef9864fed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 10V, Negative-QTOFsplash10-000i-0290000000-72d51ba5728ad3048a1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 20V, Negative-QTOFsplash10-000i-1960000000-7be39e33eed6781c50f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aromadendrin 40V, Negative-QTOFsplash10-0a73-5910000000-a72844280b3dd1d0350e2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002806
KNApSAcK IDC00007234
Chemspider ID109514
KEGG Compound IDC00974
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAromadendrin
METLIN IDNot Available
PubChem Compound122850
PDB IDNot Available
ChEBI ID15401
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1539021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .